Writing your first letter
The first letter is the hardest. You're writing to someone you've never met, you want to be encouraging without being corny, friendly without being weird, and you don't know what they'll think of you. That's normal. Everyone feels that way.
Here's the structure that works for most first letters:
- Introduce yourself, briefly. Your first name, where you live (just the state — never your full address), what you do (general — "I work in healthcare" not your employer's name), and one or two interests. Two or three sentences total.
- Tell them why you're writing. "I'm writing through Jeff's Second Family because I read your introduction letter and it stuck with me." Be honest. They can tell when you're not.
- Respond to something specific from their intro letter. Did they mention they like to draw? Read? Their faith? Their family? Pick one thing they wrote about and ask a follow-up question or share something related from your own life.
- Share one ordinary thing. What you did this weekend, something funny your kid said, a meal you cooked, the weather. Keep it real.
- Close warmly, not stiffly. "Looking forward to hearing back from you" is fine. "Praying for you in this season" is fine if it's authentic. "I hope this letter finds you well" sounds like a robot. Avoid that.
Aim for one full page, handwritten if you're using mail, or about 250–400 words if you're using a digital platform. Less than that feels like you didn't try. More than that on a first letter feels overwhelming.
What to say
The thing most first-time pen pals get wrong is overthinking the content. They want to send something meaningful — and meaningful, to them, sounds like a deep thought or a Bible verse or an inspirational quote.
What inmates actually crave is ordinary. The world they're in is the same color, the same sounds, the same routine, day after day. The most precious thing you can send is a window into a life that looks different.
Topics that work consistently well
- Daily life, in detail. What you cooked, what the dog did, the weather, your commute, what's growing in your garden, what you're watching on TV.
- Books, music, movies. If they mentioned a favorite, ask why. If you discover something new, share it. Many inmates have huge amounts of reading time and love book recommendations.
- Memories. A trip you took years ago. A grandparent's recipe. The summer you broke your arm. Specific, sensory, real.
- Their interests. If they wrote that they love drawing, ask what kind. Watercolors? Pencil? Comics? People light up when someone takes a real interest.
- Questions about them. Open ones, not interrogations. "What does a typical Tuesday look like for you?" is good. "What did you do to end up in there?" is not.
- Faith, if it's authentic. If you're a person of faith and they are too, prayer, Scripture, and reflections all welcome. Don't fake it.
- Plans. What you're hoping to do this summer. What you're working on. What you'd love to learn next.
What not to say
✓ Do
- Be specific (not "we had dinner" — say what you ate)
- Ask follow-up questions
- Share photos when allowed
- Reference what they wrote in their last letter
- Be honest about your pace
- Treat them like a friend, because they are one
✗ Don't
- DO NOT open with "I'm so sorry you're going through this"
- DO NOT ask about their case unless they bring it up first
- DO NOT try to fix them or counsel them
- DO NOT promise frequency you can't keep
- DO NOT share your home address, phone, employer, or e-mail address
- DO NOT send anything that violates platform rules (more below)
Two more things to avoid that don't fit neatly in a list:
Don't moralize. Even if they tell you something they did or are struggling with. Their lawyer, the courts, and the system have all weighed in. They don't need another voice telling them they should have done better. Your job is to be a friend, not a judge.
Don't disappear. If you decide not to continue the correspondence, end it through your dashboard so the ministry can let them know respectfully. Never just stop writing. Mail call where their name doesn't get called for weeks, after a relationship started, is one of the most painful things you can do to someone in prison.
A sample first letter
Here's roughly what a first letter looks like when it lands well. Names changed, but this is close to a real one.
Hi Marcus,
My name is Sarah and I'm writing through Jeff's Second Family. I'm in my late thirties, I live in northern Michigan, and I work as a nurse in a small clinic. I have two dogs and zero patience for cold weather, even though I've lived here my whole life.
I read your introduction letter last week and what stuck with me was when you wrote about teaching yourself guitar from a book your mom sent you. I tried to learn guitar twice in my twenties and gave up both times — partly because I had so many other distractions, partly because I was bad at it. The fact that you've stuck with it for years now, with no internet to look up tutorials, says something about you that's hard to fake.
What kind of music do you play? I grew up on Springsteen and Tom Petty in my dad's old pickup, but lately I've been listening to a lot of bluegrass — Tyler Childers especially. Do they let you listen to music in there?
This past weekend I made my grandmother's apple pie for the first time. It's one of those recipes where everything is approximate — "a handful of flour," "enough sugar." It came out lopsided but tasted right. The dogs got the crust trimmings.
I'd love to hear back from you when you have time. No pressure on the timing — I can imagine mail call works at a different pace than my email.
Take care,
Sarah
What that letter does well: introduces her without giving away identifying info, references something specific from his intro letter (the guitar), shares an ordinary detail (the pie), asks an open question, and closes without being saccharine.
Platforms by state
The platform you'll use depends on what state the inmate is in and what the prison allows. Your dashboard tells you exactly which one applies for your match. Here's the quick reference:
| Platform | Where it's used | Format | Cost |
|---|---|---|---|
| Securus | Texas (and many other state systems) | Electronic messages, sometimes with photos | ~$0.05–$0.50 per message |
| TextBehind | Many county jails and some state systems | You type online, they print and deliver | $0.50–$1.50 per letter |
| GettingOut | Some state and county systems (run by GTL/ViaPath) | Electronic messages | ~$0.10–$0.40 per message |
| CORRLINKS | Federal Bureau of Prisons (BOP) | Email-style messages | ~15¢ per message + 30¢ per photo (non-Federal inmates), paid by the volunteer |
| ConnectNetwork | Many state and county systems (also run by ViaPath/GTL — sibling to GettingOut) | Electronic messages, deposits, phone funding | ~$0.25 per message (1 credit = 1 message) |
| SMARTINMATE (Smart Communications) | Several state systems (esp. mail-replacement programs) | You upload mail, they scan and deliver; photos supported | ~$0.50 per message (50 credits) + 100 credits per photo |
| USPS (regular mail) | Many state and federal facilities still accept it | Handwritten or printed letters | One stamp + envelope |
Each platform has its own quirks — character limits, photo rules, prohibited topics. The volunteer dashboard has step-by-step setup guides for each one. We won't make you figure them out alone.
Formatting rules that apply almost everywhere
Whatever platform you use, these rules apply at most facilities:
- No staples, paper clips, or tape on physical mail. Many facilities reject anything with metal.
- No stickers, glitter, perfume, or anything that could conceal contraband.
- No Polaroid photos. Some facilities only accept printed photos because Polaroids can be tampered with.
- Limit photos to 4–5 per envelope for physical mail; some facilities cap it lower.
- No nudity, weapons, drugs, gang symbols, or anything else that the prison would reject. This includes images.
- Spaces count as characters for character limits on most digital platforms. A 4,000-character limit gets eaten faster than you'd expect.
- Don't include cash, gift cards, or anything that looks like it. Money goes through commissary deposits, never inside a letter.
- Always use the ministry's return address — never your home. This is the only approved return address. Write it exactly like this, with your own first name on the ATTN line:
Jeff's Second Family PenPal Ministry
c/o Food For Children, Inc.
70-22 165th Street
Flushing, NY 11365
ATTN: (Your FIRST NAME goes here)
Everything you write to an inmate is read by prison staff or the platform's compliance team before it reaches them. Same for everything they write to you. This isn't something to be paranoid about — it's just reality. Write like you'd write any letter that someone else might read, and you'll be fine.
When their replies are hard to read
This catches first-time pen pals off guard, so it's worth saying plainly: the replies you get back may sometimes be hard to read.
Hard in the literal sense — the handwriting, especially from older inmates or those with limited education, can be a workout. Hard in the emotional sense — they may write about loneliness, grief, regret, hope, or fear that doesn't have anywhere else to go. Hard in the spiritual sense — sometimes the gap between your life and theirs feels enormous, and you don't know what to say back.
What helps:
- Read it twice before responding. First time, just take it in. Second time, look for what they're asking for — connection, a specific question answered, just to be heard.
- You don't have to fix it. If they share something painful, you can acknowledge it without solving it. "I read what you wrote about your daughter. I can't imagine. Thank you for trusting me with that." Then keep writing about ordinary life.
- If something concerns you, tell the ministry. If you're worried about their safety or yours, contact us through your dashboard. We've handled these situations before.
- Take a break if you need one. A few days between reading and responding is fine. You don't have to fire back the same day.
Staying faithful long-term
The hardest part of pen pal ministry isn't the first letter. It's the twentieth.
The first letter is exciting. So is the first reply. By month four or five, the novelty has worn off, your life has gotten busier, and writing the next letter feels more like an obligation than a calling. This is the moment most pen pals quietly stop.
Here's how to make it past that point:
- Pick a rhythm and stick to it. The first Saturday of every month. The Sunday after church. Whatever fits your life. Calendar it.
- Use the Letter Log in your dashboard. Track when you sent and when they replied. It helps you see the rhythm of the friendship and notice when it's been too long.
- Save a folder of their letters. Re-read it before writing back. You'll catch threads you forgot — their daughter's birthday coming up, the book they were trying to find, the medical thing they mentioned in passing.
- Keep the letters short when life is full. A half-page note is better than a long letter you keep putting off because you don't have time to write it.
- Remember why you started. Most pen pals who quit do so quietly, not because they decided to, but because they drifted. The ministry sends occasional reminders. Don't ignore them.
If you do this faithfully — even at a slow pace — over months and years, something happens that's hard to describe. The person on the other end stops being "an inmate" and starts being someone you genuinely care about. The letters get easier to write because you're just catching up with a friend. And one day you realize you're not doing this as ministry anymore. You're doing it because they're part of your life.
That's the goal. Friendship is the thing.